Daily Leader Dilemmas

⏱ 6 min read

In a rush? Here is the quick overview.

The issue

• When a veteran top producer hits a slump, the impact can extend well beyond that individual.
• The way you respond is high stakes because it can either rebuild confidence and trust or damage the relationship long-term.

Best practices for you as the leader

• Start with the assumption that an established producer can recover with the right support.
• Approach the first conversation with curiosity rather than criticism, then use coaching, performance trends, and targeted observation to understand what has changed.
• Build the recovery plan with the salesperson rather than imposing it on them.

Key takeaway

Your response to a top producer’s slump can either deepen the problem or help shorten it.

Come alongside them as a coach and partner while remaining clear about expectations and accountability.

The Problem at Hand

Your top producer has hit a slump.

They have the yips. They are whiffing the ball. Whatever you like to call it, the deals simply are not coming in.

And it is stressful.

It is stressful for the salesperson, who may not understand why the methods that worked for years are suddenly producing different results.

It is also stressful for you.

A top producer may represent a significant portion of your team’s business. When their performance drops, the team goal can suddenly feel much less attainable.

That is often when the worried leader’s internal dialogue begins:

• Are they even trying?
• Have they become too comfortable?
• Do I need to get tougher?

Maybe. But not yet.

The LeDev Advice

Your first response matters. It can rebuild confidence and trust, or it can leave a previously committed employee feeling unappreciated and defensive.

Before you take action, take a breath.

An Important Distinction

This article is specifically about an established, historically successful salesperson who has entered a slump.

A new salesperson who is not ramping, an inconsistent middle performer, or an early-career rep who had one strong quarter would require a different leadership approach.

With a proven veteran, your objective is to understand what has changed, shorten the downturn, and help them regain momentum.

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Start with the Right Assumption

Earlier in my career, I worked in an organization with unusually low turnover.

Because it took approximately three years for a salesperson to build a mature book of business, we had many experienced producers who had been with the company for five, ten, or even twenty years.

Over time, we noticed an interesting pattern.

One veteran might have an exceptional year after landing a major client, while another experienced their first meaningful downturn. The following year, their positions might reverse. One would be rebuilding while the other came roaring back.

The lesson was not that veteran performance should be ignored or expected to remain flat.

The lesson was that even very successful salespeople experience natural peaks and valleys.

A slump does not automatically mean that a proven salesperson has stopped caring, lost their ability, or needs to be managed out.

In many cases, it means they need help diagnosing what has changed.

Start there.

Assume that this is a temporary downturn and that your salesperson is capable of recovering.

Your job is to help minimize the depth of the slump and shorten the time they spend in it.

That requires you to approach the situation as a coach and supporter—not as an irritated boss looking for someone to blame.

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A Cautionary Tale

I once worked with a twelve-year veteran whom we will call Charlie.

Charlie was a top-five producer, a consistent President’s Club winner, and a highly respected member of the organization.

Then he entered a deep slump.

We were not entirely sure what was happening, and neither was he. We knew he had some distractions at home and did not seem quite like himself, but he continued showing up and putting in effort.

After several difficult weeks, the division president approached him.

“I don’t know what your deal is, but you need to get it together. You need to work harder. Remember when you used to work Saturdays? Where’s that guy? You need to stop leaving at 5:30 and get back to the grind.”

Then he walked away.

Charlie’s slump continued.

A couple of weeks later, the group president invited him for coffee.

“Charlie, I’m concerned about you. I see that your numbers are down, and I’m sure this must be difficult. What do you think is happening, and how can we help?”

Charlie opened up.

They talked honestly about what he was experiencing. The group president listened, offered a few observations, gave him encouragement, and reminded him that he was valued.

Charlie eventually worked his way out of the slump—and then some. He moved from the number-five position to number two and remained there for quite some time.

Later, Charlie told me that the division president’s comments had left him so deflated that he began mentally checking out. He contacted friends at competing companies and started considering other opportunities.

The coffee conversation changed that.

He felt seen, appreciated, and supported. He re-engaged, refocused, and rebuilt his business.

The Important Plot Twist

During that supportive conversation, the group president also asked:

“Charlie, do you think you might be able to put forth a little more effort?”

Then he sat back and listened.

Charlie answered honestly: “Yeah.”

Both leaders wanted to communicate essentially the same message.

The difference was in the approach.

One delivered judgment and walked away.

The other expressed concern, asked questions, listened, and then introduced accountability within the context of support.

He did not avoid the performance issue. He simply addressed it without damaging the relationship.

That is the balance you are looking for.

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Have the Conversation First

When you notice a veteran producer’s numbers beginning to decline, do not begin by issuing warnings or prescribing solutions.

Begin with a conversation.

Invite them to coffee or find another setting where you can talk without distractions.

You might say:

“I’ve noticed that things have been more difficult lately, and I imagine that must be frustrating. What are you seeing?”

Then listen.

Do not rush to fill the silence. Do not immediately correct their explanation or turn the meeting into a lecture.

Ask thoughtful follow-up questions:

• What feels different right now?
• Where are deals getting stuck?
• What has changed in your workflow, customers, territory, or motivation?
• What have you already tried?
• Where could additional support help?

Sometimes that conversation is enough to uncover the issue and begin the recovery.

Often, however, you will need to go further.

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Build the Recovery Plan Together

One mistake leaders make is assuming that highly experienced salespeople no longer need coaching.

"Hey, Charlie, if you need me I'm over here coaching the newbie."

They do.

Veteran salespeople can develop habits that no longer serve them. They may take shortcuts, abandon strategies that once produced results, or become discouraged after a few unsuccessful attempts.

Their coaching may need to look different from the coaching you provide to a new salesperson, but it should not disappear.

If you have been holding regular coaching conversations, you may already understand where the slump began.

If you have not, now is the time to start.

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Look at the full performance picture

Begin by reviewing the data, but do not focus only on final results.

Look at the leading indicators and activity patterns underneath those results.

Compare their current performance with previous successful periods:

• Are they creating fewer new opportunities?
• Has their conversion rate changed?
• Are deals stalling at a particular stage?
• Has follow-up slowed?
• Has the quality or mix of their pipeline changed?
• Are they relying too heavily on existing customers or familiar channels?

Use meaningful trends rather than reacting to a single bad week. Four-, eight-, or thirteen-week comparisons will usually tell you more than a very short snapshot.

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Observe with a purpose

Once the data suggests where the breakdown may be occurring, use targeted observation to explore it.

You might:

• Shadow relevant sales activity.
• Listen to recorded calls.
• Review CRM notes and follow-up patterns.
• Role-play a challenging part of the sales process.
• Examine proposals, emails, or pipeline strategy.
• Compare current behaviors with periods when the salesperson was performing well.

The purpose is not to catch them doing something wrong.

You are not searching for a smoking gun.

You are trying to diagnose what has changed so that you can help them correct it.

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Agree on the next steps

Once you have gathered enough information, sit down together.

Share your observations without presenting them as a verdict.

You might say:

“Here is what I’m seeing in the numbers and in the calls I reviewed. Does that match what you are experiencing?”

Invite their perspective, then build a practical recovery plan together.

The plan should identify:

• The specific behaviors or results that need to improve.
• The actions they will take.
• The support or coaching you will provide.
• How progress will be measured.
• When you will review the plan together.

Collaborating does not mean lowering expectations.

It means creating clarity and accountability while allowing an experienced employee to participate in solving the problem.

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Why This Approach Works

A respectful conversation reminds your salesperson that their years of contribution still matter.

That can be particularly important if they are feeling burned out, discouraged, overlooked, or worried that their value to the organization is disappearing along with their results.

A clear recovery plan gives them something equally important: direction.

It replaces vague pressure with specific actions.

It also establishes accountability. Your salesperson should leave the process understanding that you believe in their ability to recover—and that improvement is still expected.

Support and accountability are not opposites.

The best coaching includes both.

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When the Problem Is Deeper

Not every slump is temporary.

Sometimes an experienced salesperson has lost the desire to do the work but feels financially unable to leave.

Sometimes a major life change is affecting their capacity, availability, or priorities.

In other cases, the role, market, or organization may have changed so significantly that the salesperson no longer knows how—or wants—to adapt.

These situations may become apparent during your initial conversation or as you work through the recovery plan.

When the issue extends beyond a straightforward performance slump, involve your leader or HR partner. Personal circumstances, accommodations, burnout, role fit, and formal performance management require thoughtful handling.

Do not try to navigate those waters alone.

Summary